Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of 1H-Pyrrolo [1, 2-α] indole Derivatives. III. Synthesis of 2, 3-Dihydro-7-hydroxy-6, 9-dimethyl-5, 8-dioxo-1H-pyrrolo [1, 2-α] indole
TOYOZO TAKADAMITSUO AKIBA
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1972 Volume 20 Issue 8 Pages 1785-1792

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Abstract
The compound related to mitomycin B, 2, 3-dihydro-7-hydroxy-6, 9-dimethyl-5, 8-dioxo-1H-pyrrolo [1, 2-α] indole (III), was synthesized starting from 2, 3, 9, 9a-tetrahydro-6, 9-dimethyl-7-nitro-1H-pyrrolo [1, 2-α] indole (II) via 2, 3-dihydro-6, 9-dimethyl-7-nitro-1H-pyrrolo [1, 2-α] indole (X), 7-amino-2, 3-dihydro-6, 9-dimethyl-1H-pyrrolo [1, 2-α] indole (XI), and 2, 3-dihydro-6, 9-dimethyl-7, 8-dioxo-1H-pyrrolo [1, 2-α] indole (VII). Some considerations were made on the mechanism of the formation of the dimers, 2, 3-dihydro-5-(2', 3', 9', 9a'-tetrahydro-6', 9'-dimethyl-1H-pyrrolo [1, 2-α] indol-7'-imino)-6, 9-dimethyl-7, 8-dioxo-1H-pyrrolo [1, 2-α] indole (VIII) and 2, 3-dihydro-5-(2', 3'-dihydro-6', 9'-dimethyl-1H-pyrrolo [1, 2-α] indol-7'-imino)-6, 9-dimethyl-7, 8-dioxo-1H-pyrrolo [1, 2-α] indole (IX), obtained by the oxidation of 7-amino-2, 3, 9, 9a-tetrahydro-6, 9-dimethyl-1H-pyrrolo [1, 2-α] indole (V) with Fremy's salt.
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© The Pharmaceutical Society of Japan
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